Intramolecular hetero-Diels-Alder reaction of N-arylimines : applications to the synthesis of octahydroacridine derivatives

Laschat, Sabine; Lauterwein, Jürgen

Intramolecular hetero-Diels-Alder reaction of N-arylimines : applications to the synthesis of octahydroacridine derivatives

dc.contributor.author	Laschat, Sabine	de
dc.contributor.author	Lauterwein, Jürgen	de
dc.date.accessioned	2009-07-17	de
dc.date.accessioned	2016-03-31T11:41:35Z
dc.date.available	2009-07-17	de
dc.date.available	2016-03-31T11:41:35Z
dc.date.issued	1993	de
dc.date.updated	2013-05-13	de
dc.description.abstract	A new intramolecular Lewis acid catalyzed hetero-Diels-Alder reaction of N-arylimines 5 with nonactivated olefins tethered to the 2-azadiene system was developed in order to prepare 1,2,3,4,-4a,9,9a,l0-octahydroacridined erivatives 6. Both reactivity and cis/ trans selectivity of 6 were mainly dependent on the substitution pattern in the 3-position of the cyclization precursor 5. The type of Lewis acid plays only a minor role in determination of the cis/trans ratio. The synthetic utility of this new cyclization was increased by performing it as a one-pot reaction. Both absolute configuration and preferred conformation were assigned by detailed NMR studies.	en
dc.identifier.other	314565329	de
dc.identifier.uri	http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-41411	de
dc.identifier.uri	http://elib.uni-stuttgart.de/handle/11682/6992
dc.identifier.uri	http://dx.doi.org/10.18419/opus-6975
dc.language.iso	en	de
dc.rights	info:eu-repo/semantics/openAccess	de
dc.subject.classification	Diels-Alder-Reaktion , Acridinderivate	de
dc.subject.ddc	540	de
dc.title	Intramolecular hetero-Diels-Alder reaction of N-arylimines : applications to the synthesis of octahydroacridine derivatives	en
dc.type	article	de
ubs.fakultaet	Fakultätsübergreifend / Sonstige Einrichtung	de
ubs.institut	Sonstige Einrichtung	de
ubs.opusid	4141	de
ubs.publikation.source	Journal of Organic Chemistry 58 (1993), S. 2856-2861. URL http://dx.doi.org./10.1021/jo00062a033	de
ubs.publikation.typ	Zeitschriftenartikel	de

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